3-(5-((2-(Dimethylamino)ethyl)(methyl)amino)pyridin-2-ylamino)-1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2(1H)-one → 10-{5-Fluoro-3-[5-({5-[4-(2-fluoroethyl)piperazin-1-yl]pyridine-2-yl}amino)-1-methyl-6-oxo-1,6-dihydropyridin-3-yl]-2-(acetoxymethyl)phenyl}-4,4-dimethyl-1,10-diazatricyclo[6.4.0.02,6]dodeca-2(6),7-dien-9-one

HRID 1919079Notes

Reaction equation

HRID 1919079 reaction equation
Br[C:2]1[CH:3]=[C:4]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][F:25])[CH2:19][CH2:18]3)=[CH:13][N:12]=2)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1.CN(C)CCN(C)C1C=CC(NC2C(=O)N(C)C=C(B3OC(C)(C)C(C)(C)O3)C=2)=NC=1.[C:57]([O:60][CH2:61][C:62]1[C:67]([N:68]2[CH2:79][CH2:78][N:77]3[C:70](=[CH:71][C:72]4[CH2:73][C:74]([CH3:81])([CH3:80])[CH2:75][C:76]=43)[C:69]2=[O:82])=[CH:66][C:65]([F:83])=[CH:64][C:63]=1Br)(=[O:59])[CH3:58]>>[F:83][C:65]1[CH:64]=[C:63]([C:2]2[CH:3]=[C:4]([NH:10][C:11]3[CH:16]=[CH:15][C:14]([N:17]4[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][F:25])[CH2:19][CH2:18]4)=[CH:13][N:12]=3)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=2)[C:62]([CH2:61][O:60][C:57](=[O:59])[CH3:58])=[C:67]([N:68]2[CH2:79][CH2:78][N:77]3[C:70](=[CH:71][C:72]4[CH2:73][C:74]([CH3:80])([CH3:81])[CH2:75][C:76]=43)[C:69]2=[O:82])[CH:66]=1

Participants

4

Reactant 3

HCID 580436803-(5-((2-(Dimethylamino)ethyl)(methyl)amino)pyridin-2-ylamino)-1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2(1H)-oneHCID 580438405-Bromo-3-(5-(4-(2-fluoroethyl)piperazin-1-yl)pyridin-2-ylamino)-1-methylpyridin-2(1H)-oneHCID 670163042-Bromo-4-fluoro-6-(9-oxo-4,4-dimethyl-1,10diazatricyclo[6.4.0.02,6]-dodeca-2(6),7-dien-10-yl)benzyl Acetate

Product 1

HCID 8666125810-{5-Fluoro-3-[5-({5-[4-(2-fluoroethyl)piperazin-1-yl]pyridine-2-yl}amino)-1-methyl-6-oxo-1,6-dihydropyridin-3-yl]-2-(acetoxymethyl)phenyl}-4,4-dimethyl-1,10-diazatricyclo[6.4.0.02,6]dodeca-2(6),7-dien-9-oneYield 33%

Procedure

Following Example 186f, 273a (which was prepared in situ from 217d using conditions analogous to those used to prepare 270d) (200 mg, 0.49 mmol) and 189a (176 mg, 0.39 mmol) were reacted to give 273b (115 mg, 33% yield).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-18539c4b0e984ebb8b1088db102ddefc
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

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